The present invention relates to cyclic carbonyl monomers functionalized with carbohydrate moieties, ring opening polymers derived therefrom, and methods of preparation of the monomers and the polymers.
Biocompatible and biodegradable polymers that assemble into well-defined nanostructures such as micelles are of increasing interest as a means for drug transport and release. Moreover, polymers bearing pendant carbohydrates, specifically sugars, are particularly useful for applications that require the targeting of carbohydrate-binding proteins known as lectins. Protein-carbohydrate interactions mediate a number of biological processes, including cell growth, inflammation, infections and adhesion, via multivalent interactions. The enhancement in binding as a consequence of polyvalent interactions is known as the glycoside cluster effect. Carbohydrate-bearing polymers provide a platform for presenting multiple copies of a saccharide simultaneously, thus enhancing their affinity and selectivity for lectins.
A number of carbohydrate-bearing polymers have been developed including dendrimers, linear polymers, and micelles. Expanding the number of monomers useful in forming carbohydrate-bearing polymers is an ongoing need, directed toward achieving polymers having a wide range of tailorable solution, physical and mechanical properties.